Skip to main content
SpringerLink
Log in

Phenolic Metabolites in Leaves of the Invasive Shrub, Lonicera maackii, and Their Potential Phytotoxic and Anti-Herbivore Effects

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

Lonicera maackii is an invasive shrub in North America for which allelopathic effects toward other plants or herbivores have been suspected. We characterized the major phenolic metabolites present in methanol extracts of L. maackii leaves. In addition, we examined the effects of methanol–water extracts of L. maackii leaves on seed germination of a target plant species and on feeding preference and growth rate of a generalist insect herbivore. A total of 13 individual major and minor compounds were detected in crude leaf extracts by high-performance liquid chromatography coupled to electronspray ionization-tandem mass spectrometry (ESI-MS/MS). Extracts were dominated by two major flavones, apigenin and luteolin, and their glucoside derivatives, apigenin-7-glucoside and luteolin-7-glucoside. Quantities of these compounds, along with chlorogenic acid, varied between two sampling points. Leaf extracts that contained these compounds were inhibitory to seed germination of Arabidopsis thaliana. In addition, treatment of artificial diet with leaf extracts deterred feeding of the generalist herbivore, Spodoptera exigua, in choice experiments but had no effect on growth rate in short-term no-choice bioassays. Purified apigenin tended to deter feeding by S. exigua and inhibited seed germination of A. thaliana. We conclude that leaves of L. maackii contain phenolic compounds, including apigenin and chlorogenic acid, capable of having biological effects on other plants and insects.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Agrell, J., Oleszak, W., Stochmal, A., Olsen, M., and Andersen, P. 2003. Herbivore-induced responses in alfalfa (Medicago sativa). J. Chem. Ecol. 29:303–320.

    Article  CAS  Google Scholar 

  • Baerson, S. R., Sanchez-Moreiras, A., Pedrol-Bonjonch, N., Schulz, M., Kagan, I. A., Agarwal, A. K., eigosa, M. J., and Duke, S. O. 2005. Detoxification and transcriptome response in Arabidopsis seedlings exposed to the allelochemical benzoxazolin-2(3H)-one. J. Biol. Chem. 280:21867–21881.

    Article  PubMed  CAS  Google Scholar 

  • Bais, H. P., Vepachedu, R., Gilroy, S., Callaway, R. M., and Vivanco, J. M. 2003. Allelopathy and exotic plant invasion: from molecules and genes to species interactions. Science. 301:1377–1380.

    Article  PubMed  CAS  Google Scholar 

  • Bais, H. P., Walker, T. S., Stermitz, F. R., Hufbauer, R. A., and Vivanco, J. M. 2002. Enantiomeric-dependent phytotoxic and antimicrobial activity of (±)-catechin. A rhizosecreted racemic mixture from spotted knapweed. Plant Physiol. 128:1173–1179.

    Article  PubMed  CAS  Google Scholar 

  • Blum, U. 1998. Effects of microbial utilization of phenolic acids and their phenolic acid breakdown products in allelopathic interactions. J. Chem. Ecol. 24:685–708.

    Article  CAS  Google Scholar 

  • Blum, U., and Gerig, T. M. 2006. Interrelationships between p-coumaric acid, evapotranspiration, soil water content, and leaf expansion. J. Chem. Ecol. 32:1573–1561.

    Article  CAS  Google Scholar 

  • Bonello, P., and Blodgett, J. T. 2003. Pinus nigra-Sphaeropsis sapinea as a model pathosystem to investigate local and systemic effects of fungal infection of pines. Physiol. Mol. Plant Pathol. 63:249–261.

    Article  Google Scholar 

  • Callaway, R. M., and Aschehoug, E. T. 2000. Invasive plants versus their new and old neighbors: a mechanism for exotic plant invasion. Science. 290:521–523.

    Article  PubMed  CAS  Google Scholar 

  • Chaves, N., Sosa, T., and Escudero, J. C. 2001. Plant growth inhibiting flavonoids in exudate of Cistus ladanifer and in associated soils. J. Chem. Ecol. 27:623–631.

    Article  PubMed  CAS  Google Scholar 

  • Collier, M. H., Vankat, J. L., and Hughes, M. R. 2002. Diminished plant richness and abundance below Lonicera maackii, an invasive shrub. Am. Mid. Nat. 147:60–71.

    Article  Google Scholar 

  • Cipollini, D., Stevenson, R., and Cipollini, K. 2008. Contrasting effects of allelochemicals from two invasive plants on the performance of a non-mycorrhizal plant. Intl. J. Plant. Sci., in press.

  • Clifford, M. N., Wu, W. G., and Kuhnert, N. 2006. The chlorogenic acids of Hemerocallis. Food Chem. 95:574–578.

    Article  CAS  Google Scholar 

  • Dorning, M., and Cipollini, D. 2006. Leaf and root extracts of the invasive shrub, Lonicera maackii, inhibit seed germination of three herbs with no autotoxic effects. Plant Ecol. 184:287–296.

    Article  Google Scholar 

  • Dowd, P. F., and Vega, F. E. 1996. Enzymatic oxidation products of allelochemicals as a basis for resistance against insects. Nat. Toxins. 4:85–91.

    Article  PubMed  CAS  Google Scholar 

  • Eyles, A., Jones, W., iedl, K., Cipollini, D., Schwartz, S., Chan, K., Herms, D., and Bonello, P. 2007. Comparative phloem chemistry of Manchurian (Fraxinus mandshurica) and two North American ash species (F. americana and F. pennsylvanica). J. Chem. Ecol. 33:1430–1448.

    Article  PubMed  CAS  Google Scholar 

  • Flamini, G., Braca, A., Cioni, P. J., and Morelli, I. 1997. Three new flavonoids and other constituents from Lonicera implexa. J. Nat. Prod. 60:449–452.

    Article  CAS  Google Scholar 

  • Graf, B. A., Milbury, P. E., and Blumberg, J. B. 2005. Flavonols, flavones, flavanones, and human health: epidemiological evidence. J. Med. Food. 8:281–290.

    Article  PubMed  CAS  Google Scholar 

  • Haribal, M., and enwick, J. A. A. 1998. Isovitexin 6″″-O-β-D-glucopyranoside: a feeding deterrent to Pieris napi oleracea from Alliaria petiolata. Phytochemistry. 47:1237–1240.

    Article  CAS  Google Scholar 

  • Harrington, R. A., Brown, B. J., and eich, P. B. 1989. Ecophysiology of exotic and native shrubs in Southern Wisconsin. Oecologia. 80:356–367.

    Article  Google Scholar 

  • Hierro, J. L., and Callaway, R. W. 2003. Allelopathy and exotic plant invasion. Plant Soil. 256:29–39.

    Article  CAS  Google Scholar 

  • Hutchinson, T. F., and Vankat, J. L. 1997. Invasibility and effects of Amur honeysuckle in southwestern Ohio forests. Cons. Biol. 11:1117–1124.

    Article  Google Scholar 

  • Hvattum, E. 2002. Determination of phenolic compounds in rose hip (Rosa canina) using liquid chromatography coupled to electrospray ionisation tandem mass spectrometry and diode-array detection. Rapid Comm. Mass Spec. 16:655–662.

    Article  CAS  Google Scholar 

  • Iwashina, T. 2003. Flavonoid function and activity to plants and other organisms. Biol. Sci. Space. 17:24–44.

    Article  PubMed  Google Scholar 

  • Maatta, K. R., Kamal-Eldin, A., and Torronen, A. R. 2003. High-performance liquid chromatography (HPLC) analysis of phenolic compounds in berries with diode array and electrospray ionization mass spectrometric (MS) detection: Ribes species. J. Agric. Food. Chem. 51:6736–6744.

    Article  PubMed  CAS  Google Scholar 

  • Markham, K. R. 1982. Techniques of flavonoid identification. Academic, London.

    Google Scholar 

  • Oberdorster, E., Clay, M. A., Cottam, D. M., Wilmot, F. A., McLachlan, J. A., and Milner, M. J. 2001. Common phytochemicals are ecdysteroid agonists and antagonists: a possible evolutionary link between vertebrate and invertebrate steroid hormones. J. Steroid Biochem. Mol. Biol. 77:229–238.

    Article  PubMed  CAS  Google Scholar 

  • Pennacchio, M., Jefferson, L., and Havens, K. 2005. Arabidopsis thaliana: A new test species for phytotoxic bioassays. J. Chem. Ecol. 31:1877–1885.

    Article  PubMed  CAS  Google Scholar 

  • Ridenour, W. M., and Callaway, R. M. 2001. The relative importance of allelopathy in interference: the effects of an invasive weed on a native bunchgrass. Oecologia. 126:444–450.

    Article  Google Scholar 

  • Rodriguez, B., odriguez, B., de la Torre, M. C., Simmonds, M. S. J., and Blaney, W. M. 1999. From a phagostimulant natural product to semisynthetic antifeedants against Spodoptera littoralis larvae: chemical transformations of the neoclerodane diterpenoid scutelgalin B. J. Nat. Prod. 62:594–600.

    Article  PubMed  CAS  Google Scholar 

  • Skulman, B. W., Mattice, J. D., Cain, M. D., and Gbur, E. E. 2004. Evidence for allelopathic interference of Japanese honeysuckle (Lonicera japonica) to loblolly and shortleaf pine regeneration. Weed Sci. 52:433–439.

    Article  CAS  Google Scholar 

  • Sripad, G., Prakash, V., and Marasing ao, M. S. 1982. Extractability of polyphenols of sunflower seed in various solvents. J. Biosci. 4:145–152.

    Article  CAS  Google Scholar 

  • Tegelberg, R., and Julkunen-Titto, R. 2001. Quantitative changes in secondary metabolites in dark-leaved willow (Salix myrsinifolia) exposed to enhanced ultraviolet-b radiation. Physiol. Plant. 113:541–547.

    Article  CAS  Google Scholar 

  • Trisel, D. E. 1997. The invasive shrub, Lonicera maackii (Rupr.) Herder (Caprifoliaceae): Factors contributing to its success and its effect on native species. PhD Dissertation, Miami University, Oxford, USA.

  • USDA, NRCS. 2007. The PLANTS Database (http://plants.usda.gov, 4 December 2007). National Plant Data Center, Baton Rouge, LA., USA.

  • Verbeek, R., Plomp, A. C., Van Tol, E. A. F., and Van Noort, J. M. 2004. The flavones luteolin and apigenin inhibit in vitro antigen-specific proliferation and interferon-gamma production by murine and human autoimmune T cells. Biochem. Pharmacol. 68:621–629.

    Article  PubMed  CAS  Google Scholar 

  • Wu, W., Yan, C. Y., Li, L., Liu, Z. Q., and Liu, S. Y. 2004. Studies on the flavones using liquid chromatography-electrospray ionization tandem mass spectrometry. J. Chrom. A. 1047:213–220.

    CAS  Google Scholar 

  • Zhu, X. F., Zhang, H. X., and Lo, R. 2004. Phenolic compounds from the leaf extract of artichoke (Cynara scolymus L.) and their antimicrobial activities. J. Agric. Food. Chem. 52:7272–7278.

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

We thank the Ohio Plant Biotechnology Consortium and Wright State University for funding. Comments by two anonymous reviewers substantially improved the manuscript.

Author information

Author notes

  1. Alieta Eyles

    Present address: Cooperative Research Centre for Forestry, TIAR/University of Tasmania, Private Bag 12, Hobart, 7001, Australia

Authors and Affiliations

  1. Department of Biological Sciences, Wright State University, 208 Biological Sciences Building, 3640 Colonel Glenn Hwy, Dayton, OH, 45435, USA

    Don Cipollini, Randall Stevenson & Stephanie Enright

  2. Department of Plant Pathology, The Ohio State University, 201 Kottman Hall, 2021 Coffey Road, Columbus, OH, 43210, USA

    Alieta Eyles & Pierluigi Bonello

Authors
  1. Don Cipollini
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Randall Stevenson
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Stephanie Enright
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alieta Eyles
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Pierluigi Bonello
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Don Cipollini.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Cipollini, D., Stevenson, R., Enright, S. et al. Phenolic Metabolites in Leaves of the Invasive Shrub, Lonicera maackii, and Their Potential Phytotoxic and Anti-Herbivore Effects. J Chem Ecol 34, 144–152 (2008). https://doi.org/10.1007/s10886-008-9426-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10886-008-9426-2

Keywords

Search

Navigation